Re: 1987 Winner 1950
Welcome aboard.
The short answer is, if this is your first boat, I would say spend the money and get something a little newer. Especially if your not looking to do some repairs right out of the gate.
Looks like Winner Boats went out of business in 1989 so don't expect to find any parts for the boat. I have never heard of them and had to really look on the internet to find out what one was. What motor is in it? If it's a base Ford then you at even a bigger disadvantage. OMC is gone and old Volvo and Mercruiser is getting hard to find parts for. Or is it an OB model?
NADA says one like it is worth about half of price. If you really want it then make them an offer contingent of a water test. I dont know where you are so if there is ice on your water like here in MI then you need to wait make the final deal once you can drive the boat. Find a friend that knows something about boats or go to a different dealer and see if they have a mechanic that is willing to go for a test ride in it. You will probably have to pay for his time, but its money well spent. Listen to what he says, if he says run away from it. DO IT!!!
To may have just bought a boat and then found they did not like it or it was a pile of junk. There are many things you need to look for and we can not list it all here. Sorry
Post your area and maybe you can get someone from here to go with you.
Good luck, let us know how things go.